GB1254724A - New chemical compound useful as starting substance for amino sugars and process for producing it - Google Patents

New chemical compound useful as starting substance for amino sugars and process for producing it

Info

Publication number
GB1254724A
GB1254724A GB4155/69A GB415569A GB1254724A GB 1254724 A GB1254724 A GB 1254724A GB 4155/69 A GB4155/69 A GB 4155/69A GB 415569 A GB415569 A GB 415569A GB 1254724 A GB1254724 A GB 1254724A
Authority
GB
United Kingdom
Prior art keywords
methyltetrahydropyran
acetamido
methyl
pyran
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB4155/69A
Inventor
Yasuji Suhara
Kenji Maeda
Hamao Umezawa
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Microbial Chemistry Research Foundation
Original Assignee
Microbial Chemistry Research Foundation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Microbial Chemistry Research Foundation filed Critical Microbial Chemistry Research Foundation
Publication of GB1254724A publication Critical patent/GB1254724A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/10—Oxygen atoms
    • C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/14—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/30—Oxygen atoms, e.g. delta-lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Saccharide Compounds (AREA)

Abstract

1,254,724. 5 - Acetamido 6 -methyltetrahydropyran-2-ol; amino sugars. ZAIDAN HOJIN BISEIBUTSU KAGAKU KENKYU KAI. 24 Jan., 1969 [31 Jan., 1968 (5); 11 Jan., 1969 (2)], No. 4155/69. Heading C2C. The novel compound, 5-acetamido-6-methyltetrahydropyran-2-ol is obtained by LiAIH 4 reduction of 5-acetamido-6-methyltetrahydropyran-2-one. The novel amide may be acetylated at temperatures below 100‹ C. with acetic anhydride in the presence of a tertiary base and the resultant compound heated ,to obtain 3- acetamido - 2 methyl - 3,4 - dihydro - 2H- pyran. Alternatively, the novel amide may be treated with acetic anhydride in the presence of a tertiary base at temperatures above 100‹ C. to obtain 3 - diacetylamino - 2 - methyl - 3,4- dihydro-2H - pyran which" on reaction with nitrosyl chloride in an organic solvent yields 2- chloro - 5 - diacetylamino - 6 - methyl - 3 - nitrosotetrahydropyran dimer. This dimer reacts with alcohols or polyols of the formula ROH, where R is an optionally hydroxyl substituted hydrocarbon radical to form dimers of the formula which on reduction, e.g. catalytic hydrogenation, and acid hydrolysis yield amines of the formula which may be further hydrolysed, e.g. with Ba(OH) 2 , to a 2,4-diamino-2,3,4,6-tetradeoxyarabino-hexopyranoside of the formula In examples, the preparation of methyl, ethyl, iso-propyl and inosityl pyranosides (derivatives of kasugaminide) is described. 5 - Acetamido - 6 - methyltetrahydropyran - 2- one is prepared by treating 6-methyl-3,4-dihydro-2H-pyran-2-one with nitrosylchloride to obtain the dimer of 6-chloro,-6-nethyl-5-nitroso,- tetrahydropyran-2-one which on acid hydrolysis yields 4-oximino-5-oa;ohexaiwic acid which is subsequently reduced to DL.erythro-4.amino.5. hydroxyhexanoic acid from which the required pyran-2-one is obtained by lactonization, e.g. using acetic anhydride. The 4-amino-5-hydroxyhexanoic acid may be N-methylated with HCHO in the presence of H 2 /Pd/C and the resultant 4 - dimethylamino 5 - hydroxyhexanoic acid lactonized to 3-dimethylamino-2- methyltetrahydropyran-5-one, characterized as the picrate. This lactone can be reduced with LiAIH 4 to 5-hydroxy-9-di'methylamino-Z-methyltetrahydropyran.
GB4155/69A 1968-01-31 1969-01-24 New chemical compound useful as starting substance for amino sugars and process for producing it Expired GB1254724A (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
JP535568 1968-01-31
JP535868 1968-01-31
JP535768 1968-01-31
JP535468 1968-01-31
JP535668 1968-01-31
JP190869 1969-01-11
JP190969 1969-01-11

Publications (1)

Publication Number Publication Date
GB1254724A true GB1254724A (en) 1971-11-24

Family

ID=27563162

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4155/69A Expired GB1254724A (en) 1968-01-31 1969-01-24 New chemical compound useful as starting substance for amino sugars and process for producing it

Country Status (7)

Country Link
US (1) US3681398A (en)
CA (1) CA931966A (en)
CH (1) CH520665A (en)
DE (1) DE1904896A1 (en)
FR (1) FR2001052A1 (en)
GB (1) GB1254724A (en)
IT (1) IT1013504B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1603609A (en) * 1977-04-14 1981-11-25 Chembiomed Ltd O-protected 2-azido-2-deoxy-glycosyl nitrates
DE112006000999A5 (en) * 2005-05-25 2008-06-19 Merck Patent Gmbh Formyltetrahydrophyrans, process for their preparation and their use in the preparation of liquid crystalline compounds

Also Published As

Publication number Publication date
DE1904896A1 (en) 1970-01-15
US3681398A (en) 1972-08-01
FR2001052A1 (en) 1969-09-19
IT1013504B (en) 1977-03-30
CA931966A (en) 1973-08-14
CH520665A (en) 1972-03-31

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PLNP Patent lapsed through nonpayment of renewal fees